Ring transformation of 1-[(1,2,4-oxadiazol-3-yl)methyl]isoquinolines into 2-acylaminopyrazolo[5,1-a]isoquinolines

Bata, Imre; Heja, G.; Kiss, Pál; Korbonits, D.

doi:10.1039/p19860000009

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1996

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Cited by 7 publications

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Synthesis of 4‐Aminopyrimidines from 1,2,4‐Oxadiazoles, V^[1]. Reductive Formation of 2‐(Benzoylamino)indole from 3‐(2‐Aminobenzyl)‐5‐phenyl‐1,2,4‐oxadiazole and Its Transformation to 6‐Phenyl‐8H‐pyrimido‐[1,6‐a: 4,5‐b']diindole, a New Heterocyclic Ring System

et al. 1993

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Catalytic hydrogenation of 5‐substituted 3‐(2‐aminobenzyl)‐1,2,4‐oxadiazoles 7 give 2‐(acylamino)indoles 10. Treatment of 2‐(benzoylamino)indoles 10a–c with acid leads to the novel 6‐phenyl‐8H‐pyrimido[1,6‐a: 4,5‐b']diindoles 19a–c. A route for the new ring formation is proposed. Catalytic hydrogenation of 19a (Raney nickel, 70°C, atmospheric pressure) saturates the 6‐phenyl ring but leaves the pentacyclic ring system intact. The structure of 19a is confirmed by an X‐ray crystallographic analysis.

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Synthesis of 4‐Aminopyrimidines from 1,2,4‐Oxadiazoles, V^[1]. Reductive Formation of 2‐(Benzoylamino)indole from 3‐(2‐Aminobenzyl)‐5‐phenyl‐1,2,4‐oxadiazole and Its Transformation to 6‐Phenyl‐8H‐pyrimido‐[1,6‐a: 4,5‐b']diindole, a New Heterocyclic Ring System

et al. 1993

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ChemInform Abstract: Ring Transformation of 1‐[(1,2,4‐Oxadiazol‐3‐yl)methyl]isoquinolines Into 2‐Acylaminopyrazolo[5,1‐a]isoquinolines.

Bata¹,

Heja²,

Kiss³

et al. 1986

Chemischer Informationsdienst

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Pyrazoles

Elguero

1996

Comprehensive Heterocyclic Chemistry II

168

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Ring transformation of 1-[(1,2,4-oxadiazol-3-yl)methyl]isoquinolines into 2-acylaminopyrazolo[5,1-a]isoquinolines

Cited by 7 publications

References 1 publication

Synthesis of 4‐Aminopyrimidines from 1,2,4‐Oxadiazoles, V^[1]. Reductive Formation of 2‐(Benzoylamino)indole from 3‐(2‐Aminobenzyl)‐5‐phenyl‐1,2,4‐oxadiazole and Its Transformation to 6‐Phenyl‐8H‐pyrimido‐[1,6‐a: 4,5‐b']diindole, a New Heterocyclic Ring System

Synthesis of 4‐Aminopyrimidines from 1,2,4‐Oxadiazoles, V^[1]. Reductive Formation of 2‐(Benzoylamino)indole from 3‐(2‐Aminobenzyl)‐5‐phenyl‐1,2,4‐oxadiazole and Its Transformation to 6‐Phenyl‐8H‐pyrimido‐[1,6‐a: 4,5‐b']diindole, a New Heterocyclic Ring System

ChemInform Abstract: Ring Transformation of 1‐[(1,2,4‐Oxadiazol‐3‐yl)methyl]isoquinolines Into 2‐Acylaminopyrazolo[5,1‐a]isoquinolines.

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Ring transformation of 1-[(1,2,4-oxadiazol-3-yl)methyl]isoquinolines into 2-acylaminopyrazolo[5,1-a]isoquinolines

Cited by 7 publications

References 1 publication

Synthesis of 4‐Aminopyrimidines from 1,2,4‐Oxadiazoles, V[1]. Reductive Formation of 2‐(Benzoylamino)indole from 3‐(2‐Aminobenzyl)‐5‐phenyl‐1,2,4‐oxadiazole and Its Transformation to 6‐Phenyl‐8H‐pyrimido‐[1,6‐a: 4,5‐b']diindole, a New Heterocyclic Ring System

Synthesis of 4‐Aminopyrimidines from 1,2,4‐Oxadiazoles, V[1]. Reductive Formation of 2‐(Benzoylamino)indole from 3‐(2‐Aminobenzyl)‐5‐phenyl‐1,2,4‐oxadiazole and Its Transformation to 6‐Phenyl‐8H‐pyrimido‐[1,6‐a: 4,5‐b']diindole, a New Heterocyclic Ring System

ChemInform Abstract: Ring Transformation of 1‐[(1,2,4‐Oxadiazol‐3‐yl)methyl]isoquinolines Into 2‐Acylaminopyrazolo[5,1‐a]isoquinolines.

Pyrazoles

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Synthesis of 4‐Aminopyrimidines from 1,2,4‐Oxadiazoles, V^[1]. Reductive Formation of 2‐(Benzoylamino)indole from 3‐(2‐Aminobenzyl)‐5‐phenyl‐1,2,4‐oxadiazole and Its Transformation to 6‐Phenyl‐8H‐pyrimido‐[1,6‐a: 4,5‐b']diindole, a New Heterocyclic Ring System

Synthesis of 4‐Aminopyrimidines from 1,2,4‐Oxadiazoles, V^[1]. Reductive Formation of 2‐(Benzoylamino)indole from 3‐(2‐Aminobenzyl)‐5‐phenyl‐1,2,4‐oxadiazole and Its Transformation to 6‐Phenyl‐8H‐pyrimido‐[1,6‐a: 4,5‐b']diindole, a New Heterocyclic Ring System